This paper is dedicated to Professor Masahiro Murakami for his contribution to science.
The reaction of phosphonates carrying a binaphthyl group with a range of Grignard
reagents was complete within two hours at 0 °C to give phosphinates carrying a hydroxybinaphthyl
group with high efficiency and diastereoselectivity. The resulting phosphinates were
further subjected to a substitution reaction with MeMgBr. The reaction at reflux temperature
in THF or toluene permitted the formation of P-chirogenic tertiary phosphine oxides
with a high enantiomeric ratio. Rare examples of P-chirogenic alkynyl phosphine oxides
were also obtained. The sequential one-pot substitution reaction of phosphonates bearing
a binaphthyl group with two different Grignard reagents successfully gave the corresponding
P-chirogenic phosphine oxides with enantiomeric ratios nearly equal to those of oxides
derived from two-step reactions.
Key words
chirogenic compounds - phosphine oxides - binaphthyl phosphonates - chirality transfer
reaction - one-pot reaction